


Watch Where You're Going

by ifyouloveme_letmebinge



Category: Supernatural
Genre: Bad Boy Dean Winchester, But it's okay, Can't Blame Cas, Cas Sets Him Right, Cas is a Sophomore, Castiel Doesn't Like Dean At First, Castiel Has Feelings for Dean Winchester, Castiel and Dean Winchester Falling in Love, Castiel and Dean Winchester Have a Profound Bond, Castiel and Dean Winchester Use Their Words, Castiel and Dean Winchester in Love, Castiel/Dean Winchester First Kiss, Castiel/Dean Winchester Mutual Pining, Comfortably Bisexual Dean Winchester, Dean Doesn't Know How To Deal With Feelings So He Gets Aggressive, Dean Is Kind Of A Bully, Dean Winchester Has a Crush on Castiel, Dean Winchester Needs a Hug, Dean Winchester is Bad at Feelings, Dean is a racer, Dean is a senior, Dean rides a motorcycle, Established Castiel/Dean Winchester, Fluff, High School, High School AU, High School Destiel AU, I Fixed It Halfway Through Because I Didn't Want To Rewrite What I Already Had, I Was Mad At S15 Chuck And It Came Through Here, It's Hard Not To Have A Crush On Dean In This One, M/M, Minor Violence, More Like Boys Being Boys, No Smut, Please They're Only In High School, They Belong Together Your Honor, Tooth-Rotting Fluff, Watch Me Make Stuff Up About Riding A Motorcycle
Language: English
Status: Completed
Published: 2020-05-09
Updated: 2020-05-09
Packaged: 2021-03-02 21:15:04
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 4,466
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24083437
Author URL: https://archiveofourown.org/users/ifyouloveme_letmebinge/pseuds/ifyouloveme_letmebinge
Summary: Castiel didn't expect his move to a new school to be all rainbows and sparkles but really, having the baddest boy of the school pick on him was just the cherry on top.>>In which Bad Boy Motorcycle Riding!Dean Winchester may or may not have a thing for Innocent Baby Who Doesn't Have Time For This!Castiel and feels ensue.***I came up with this at 6:30 in the morning during breakfast, don't yell at me. It's a Destiel High School AU and I made the gays acceptable in this school bc I love them too much to make them suffer.---- ALSOOO: if any of the beginning just seems too toxic, please let me know your thoughts on it. The absolute last thing I would want to do is make light of bullying or physical violence in a school setting because it's a serious thing. I do not condone or encourage what Dean does here in any way; neither do I agree with Cas's silence regarding it. I personally thought about it as picking on someone when you have a crush on them (like in fucking elementary school) to get their attention, but if it doesn't come across as that, please let me know.Otherwise, please enjoy our boys smack in the middle of a High School Trope!
Relationships: Castiel/Dean Winchester
Comments: 5
Kudos: 117





	1. Watch

Castiel's hair prickled on the back of his neck at the gruff voice.

"Watch where you're going!"

His right shoulder was shoved by the taller boy wearing the leather jacket. The boy who had been bullying Castiel since his first day at Lebanon High. The baddest boy of the school, Dean Winchester.

Castiel wasn't much into stereotypes and such, but he had to admit that Dean Winchester fit his perfectly. Dean was tall and handsome enough to make any girl or guy do a double take when they walked by, and he had been watching Dean. The way he charmed everyone made him sexy and mysterious. Like any "bad boy" Dean also rode a motorcycle. Castiel discovered this when he tried to run him over with it one day after classes.

Every single day, Dean Winchester plays a game Castiel likes to call "How to Dick with Cas." Dean is so far undefeated.

Dean glanced back at him with a smug smirk because he managed to get Castiel to bump into a locker when he shoved him. The little fucker.

Castiel kept his head down and quickened his strides; he needed to get out of that hallway right the fuck now.

***  
The thud of the books of the floor were covered by the ringing in Castiel's ear. Dean had just shoved him so hard, his head slammed the wall with a thuck, and he lost all ability to function, dropping his books to the ground. The papers scattered everywhere as Castiel braced himself against the wall and touched the left side of his head for any sign of blood. He sighed heavily as he found none.

Now is when the unexpected happened. Dean had stopped walking and was staring at Castiel, dizzy as he knelt on the floor beside his books. He picked everything up around them and put it back together on a pile.

Dean quickly turned around and started to walk away,"I- um. Sorry."

As he stood back up, Castiel didn't like that his History textbook was under his English binder since he had History first, but he wasn't complaining.

***  
His councilors warned him against it, but Castiel was always a bit of a rebel and couldn't resist taking AP Chem just to prove them wrong.

He was now using his free period to make up a titration lab from last week which he missed because he was at the doctors. Getting his head checked for any concussions. Because Dean pushed him.

Castiel thought about reporting it, but ultimately there was no damage, and yeah; he was sort of a weak, non-violent person which meant he wasn't used to getting pushed around like the other guys his age - he wasn't used to fights or confrontation, so it hurt him more. But he was perfectly fine. And Dean even apologized.

As well as starting to be weirdly nice to him now. Dean had stopped giving him ugly looks in the halls, and there were no more rough physical contact "accidents." Dean just winked at him and teased him with some shoulder bumps every now and then. Castiel was distraught but didn't let it take up too much of his time.

He was wearing full protective gear. Goggles and a dirty apron. He didn't understand why he didn't have to wear gloves when he was experimenting with a high concentration of hydrochloric acid, but still he was careful not to spill anything.

Just as he was cleaning the flask to start, Dean briskly walks in. He stops at the door and looks around the room, his eyes eventually settling on Castiel who stands there holding a wet glass flask and paper towel. Smug as ever, Dean smirks at him and walks closer.

"What's up nerd?" He braces his hands on the lab table, opposite Castiel who is glad for the barrier. What the fuck does Dean think he's doing?

"Make-up lab. Go away." Castiel mutters.  
Dean only smiles wider and picks up the HCl bottle, swirling it around.

" 'Hydrochloric Acid'. Hm. Sounds... smart."

Castiel won't admit it, but he wanted Dean to have a little accident with the acid and get burned. Just because he was annoying.

"So... um. I wanted to uh- well I- would you look at me?" Dean snapped.

Castiel didn't want to encourage any interaction but he felt he didn't have a choice. Dean was a little taller than him and he had much more muscle. He seemed to be gripping the edge of the lab table too hard. As Castiel's eyes moved to his face, he smirked and looked down.

"So, um. Just wondering if you've heard of the race that's gonna happen in a couple days. And if you were going."

Of course, Castiel wasn't going. It was an illegal motorcycle race around the school campus Thursday night. He had homework. But Dean's face was so sincere in asking that he doubted himself.

"I um, I don't know yet."

Dean's cheeks turned pink, "I'm just uh, may- maybe you should go. I mean, I'm going to be racing so yeah. Go. Or not if you can't."

"Okay." Castiel said slowly.

"Yeah." Dean stared at him, and Castiel didn't know if he wanted to say something or not so he was quiet. "Ye- um, yeah. Bye."

Dean quickly turned and hurried towards the door.

Castiel's stomach fluttered when Dean glanced back at him over his shoulder, before slamming into the wall with a thump.

Castiel's snort was so loud, it surprised even him. Dean recomposed himself, his hand behind his head rubbing his neck and a dark flush surfaced on his cheeks.

He chuckled dryly and cleared his throat, unsure of what to do.

"Watch where you're going." Castiel managed to say before he went into a laughing fit, clutching his stomach. He quickly stopped himself and saw Dean try to keep a smile from his radiant face. Dean awkwardly smiled before walking out with hurried footsteps.

Castiel went home that day thinking about Dean's smile. And about how he was going to sneak out on Thursday night.


	2. Where

**Summary for the Chapter:**

> Cas would rather be asleep, honestly. But then he would miss Dean looking like that...

The sounds of people yelling, drinking and having fun could be heard as Castiel walked closer to his school.

He only lived a couple of minutes away, and it was a 10 minute walk which called for a sweatshirt and his trenchcoat in the early spring weather. He didn't mind walking as it gave him time to think about his life. And the horrible decisions he has been making with it.

Taking AP Chem as a sophomore? Dumb.

Interacting with resident senior bad boy, Dean Winchester? Very dumb.

Sneaking out of his uncle Bobby's house on a Thursday night to come to an illegal motorcycle race at school just to see Dean? Stupid dumb.

No. He thought, I'm just curious. This has nothing to do with Dean. He's a dick and I hate him and he almost gave me a concussion.

Castiel reached the back parking lot and immediately felt left out. Everyone there was part of the druggie gang from all the different grades, and they were all so loud and all getting so high that he wondered how the police hadn't arrived yet. They stood in little groups, to his left there were some senior girls who passed around a blunt and Castiel's nose scrunched at the bitter smell that wafted in his face. He had never liked drugs or anything that put people under the influence.

Finally, Castiel had made up his mind, he would not just stand here to be oogled at the druggies and wait to be arrested, he would go home and get a good night's sleep for his Honors Spanish 3 past tense quiz tomorrow when he heard the memorable sound of Dean's bike behind him.

He slowly turned around and was just surprised at the relief he felt that Dean was there as he was at his shocked look when he took off his helmet. A slow smirk spread across his face and he hopped off the bike putting his helmet under his arm.

Dean wore his leather jacket, zipped up because of the chilly night air, with ripped at the knee black jeans and his normal boots. For Castiel to say he looked like a damn snack would be an understatement. The girls to his left seemed to agree as they started shouting at Dean's arrival.

Dean ignored them and walked to stop in front of Castiel, "You came."

"I did."

They stared at each other until Dean's whole face was lit with his smile and Castiel felt his skin itch.

"Is it so surprising?"

Dean's chuckle sounded quiet in the middle of the chaos around them, "Yeah. I mean, uh, you didn't seem too eager when I invited you."

"You really wanted me to come see you?"

"Winchester!" The voice behind Dean interrupted their conversation and Dean, now annoyed, turned to it.

"Shurley." Was Dean's greeting at the small guy looking tough behind them.

Chuck Shurley might be just a junior but the amount of trouble he causes is enough for a millennia. Dean is the "bad boy" in the school but Chuck is... not to be messed with.

What is Dean thinking racing against him?

"I'll see you on the finish line. That is, after I win, and if you make it there." Chuck sneered and walked away towards the starting parking spot, leaving the boys to themselves again.

"Asshole galore, that dude." Dean grumbled to Castiel.

"Look I know it's not my place but, are you sure this is a good idea?"

Dean sighed at Castiel's question and looked around him. Somehow, in the midst of all the people who were there to watch him, Castiel was the only one that mattered. The only one he really cared about. In truth, Dean only came to this stupid race because he had the smallest glimmer of hope that Castiel would also be there.

And Dean loves to show off.

"Don't worry about it, alright? You're looking at the best goddamn rider in this town," Dean lightly hit Castiel with his helmet, "There's no way I'm losing to that short bus trying to compensate for his lack of self esteem and superiority complex."

Castiel laughed loudly without knowing and Dean, amused by it, joined him. Dean felt good at that moment and took his chance by saying what had been on his mind that night.

"So I was thinking, I'm uh, gonna um, dedicate this race t-to you Castiel."

Castiel's laugh was cut short and all he could do was breathe out a perplexed "Oh."

Dean, noticing he made the moment awkward, cleared his throat and decided to get this done with, "Welp. Okay um, wish me luck. See ya."

"Dean" Castiel called him back before he could get five steps away. He turned too look over his shoulder, shyly.

"Just... watch where you're going."

"You got it." Dean smiled and put his helmet on, climbing on his bike and riding off to the set parking spot to start the race.

The circuit was easy. From the farthest parking spot in the school, five times around it, and a quarter more ending at the main parking lot at the front. Winner gets $500, the loser's bike till the end of the year and the reputation, of course.

As the crowd gathered excitedly, a skinny redhead with shorts too short for the early spring weather walked to stand in front of Dean and Chuck and their bikes. She held a bright red scarf.

As she raised it over her head, Chuck sneered as the motorcycles revved, "Anna baby, wanna get outta here after I win? I'll let you drive my sweet ride..."

The girl, Anna, seemed surprised at first then acted like she didn't even hear him, but looked happy enough to get the attention she thought she deserved from wearing those shorts. Castiel almost asked her if she wanted to wear his trench-coat, but then she brought her hand down and both racers sped away leaving a trail of smoke behind them.

**Notes for the Chapter:**

> PLAAAAAAAAAAAAAAAAAAAAAAAAAACE YOUR BETSSSSSSSSSSSSS!!!!!!!!!!!!!!!!!!!!!!!!!!!


	3. You're

**Summary for the Chapter:**

> It would be a miracle if Dean could not make Cas have severe anxiety over him, but alas...

Castiel fidgeted with his coat as he waited among the loud crowd. Some were cheering for Dean, some for Chuck. He didn't know who he should even root for.

Dean had been harassing him ever since he moved to this school, constantly making fun of him and trying to make his life hell just to get a reaction out of him. That's how it was, at least, until he stopped one day, probably realizing Castiel got legitimately hurt and not wanting to be expelled or something for it.

He didn't know what it meant or even why he went through all that trouble to then give it up completely. And then...

"I'm gonna dedicate this race to you Castiel."

But why?

And Chuck wasn't much better. In fact, Chuck was 200 times worse. His mere presence made the hairs on the back of Castiel's neck stand up, made his fight-or-flight instincts kick in, made bile rise in his throat if he passed too close. Chuck was undeniably the worst person Castiel had ever had the misfortune of meeting.

Which made his decision of rooting for Dean so much easier.

Since he had dedicated this race to him, it was only fair he took Dean's side. Castiel just hoped he would be safe.

****  
The wind hit Dean's helmet like a train, whooshing around his bike.

He was definitely not being safe.

Getting closer and closer to almost 70 miles per hour, his engine revved protests as he made some very tight curves. Around and around the school they went.

He couldn't even see Chuck anymore and he couldn't decide if that was a good or bad thing. On the final stretches of his second lap around, he heard the revs of another bike, Chuck's.

Inwardly groaning, Dean put his foot down just a bit further and felt his bike forcefully lunge forward as it picked up speed.

"Come on, Baby don't fail me now." He whispered inside his helmet, the words being left behind him as he went faster, hoping to leave his adversary behind him in the dust.

Middle of the third lap and he heard Chuck's bike just as he turned for the last leg of it across the front of the school. He tried to ignore the increasing sounds from behind him but eventually, just as he feared, he felt the other bike come up next to his.

Dean had two options: swerve into it, probably causing a bad crash for Chuck at least but also endangering himself as well, or trying to be faster than him for the rest of the race. In the midst of him deciding whether to be the bad guy or not, Chuck swerved into Dean's bike and then swerved back right before hitting it, but Dean was already startled and wiggled away, killing speed.

He shook it off and pressed his foot down; if he was going to play dirty, so would Dean.

Coming up behind Chuck he steered to the left to try and align himself with him, but Chuck swerved left. Dean's reflexes tugged him to the right but somehow so did Chuck, blocking him once again.

A lightbulb went off in Dean's head just as they finished their fourth lap, he had faith in his abilities with his motorcycle, from riding and fixing bikes since he was little with his dad but he couldn't say the same for Chuck who he knew lacked as much experience as him. He had to use Chuck's arrogance as his own demise.

If he really wanted to keep blocking him and keep thinking he was the best rider, then he would totally be able to keep control while Dean violently swerved left and right.

Right?

Wrong. It didn't take too long for his back wheel to be too slow to the catch up and lose control, he almost spun, leaving Dean to take the opportunity to pass him quickly as he begun his final lap. He heard screeching and sputtering from behind him and laughed victoriously, knowing Chuck had to stop and that there was no way he would win this race now.

****   
Castiel brunched his trench-coat tighter around himself.

The cool night air was picking up as he waited for the race to finish, bringing with it a sense of finality. He wanted to leave before he found out what exactly was ending.

His ears perked at the sound of a motorcycle - loud and annoying and clear - and he felt his whole body flood with warmth, but he couldn't get ahead of himself.

What if it was Chuck? What if Dean hadn't won?

What if he crashed and was dying and bleeding out right now, needing immediate help?

Stop it. He's fine. He always is.

Why do you care? He bullied you, stupid.

Castiel's internal monologue was interrupted by the brilliant sight of Dean riding up on his bike. No sight of Chuck behind him.

He parked on the finish line, propped up his vehicle and took his helmet off, revealing his disheveled hair and giant handsome smile. He hanged his helmet and took his leather gloves off as everyone stormed his way, positively vivid with teenage hormones feeding off his adrenaline.

They may have been cheering and screaming at the victory, but Castiel only heard static as he walked towards his champion.

The crowd opened like waves for him to walk through and he was right there.

Right in front of Dean.

The only confirmation Dean needed of how Castiel felt about this was given through his dazzling toothy smile, one that made something in Dean's heart ache to be closer.

He swung his leg off the bike, and leaned on it, raising his fists in the air to agitate the crowd, leather jacket shifting in a way that made Castiel think he looked so handsome, it was illegal.

Speaking of illegal, the party ended with a snap as they all heard police sirens in the distance closing in. Dean and Castiel's eyes bulged in their stare, and with a quick flick of a head, Castiel was hopping on the bike behind Dean and riding off into the night.

**Notes for the Chapter:**

> Cas really is a lucky bitch, huh. Dean's motorcycle is not the only thing I would want to ride...


	4. Going

**Summary for the Chapter:**

> Dean has been an asshole. But he's cute. Can Castiel forgive him?

If Castiel had told himself that he would be riding Dean Winchester's bike a week ago, he never would have believed it. At the least, he would have laughed in his own face.

If only he could see himself now.

Castiel was holding on to Dean in a tight hug from behind, and Dean didn't seem to mind as they sped away into the night, Castiel giving quiet directions to his house from behind Dean's shoulder.

The thought of how many girls had been in the same position as him flooded his brain and he grimaced and pushed it away, choosing to think of the breadth of Dean's shoulder underneath his jacket pressing into Castiel's cheek instead.

Eventually, Dean slowed the bike as he turned into Castiel's street and he turned his helmet covered head to the side as a silent question of where to stop. Castiel was entranced by the turn of his neck where a sliver of it was showing from between the helmet and the collar of his jacket. 

He tightened his arms around Dean and quietly said, "Not here, please."

Dean tensed but seemed to understand, and he steered back to a more secluded street not far away from Castiel's own, but somewhere they couldn't be seen. Castiel wasn't comfortable with the thought of his family catching him with a boy after he snuck out, he preferred to be as discreet as possible.

The bike slowed to a stop and it gave off a cough that seemed way too loud in the quiet of the neighborhood, probably due to its efforts in the race only minutes ago.

Castiel was unsure what to do. He knew he should probably let go of Dean and thank him and walk home and never interact with him again. But Castiel didn't have a single bone in his body that wanted to do that.

Dean shifted with a deep breath and, startled, Castiel pulled his arms away and clumsily stepped off the bike. Dean remained seated, with his hands in between his legs. Castiel stared at him, wanting a bolt of lightening to strike him down right there, so he wouldn't have to talk this out. Whatever this was.

After a silent moment Dean raised his hands to take his helmet off and when he found his eyes, Castiel was taken aback by how soft they were, how they glowed dimly in the street light.

He felt his own expression soften, the tension in his shoulders wash away and he gazed at Dean.

The curve of his legs on the motorcycle, knee poking out of his jeans just slightly. The relaxed way he sat on top of it with his helmet between his hands in front of him, how strong his back and shoulders looked underneath leather and the way his collar stood up to graze his jaw. His eyes followed it to the soft pout of his lips, and the upwards slant of his nose, and his eyes - so soft and sincere and too thoughtful, too intense - and Castiel felt his heartbeat in his chest as he realized he might--

"I have two things to say." Dean broke the silence. He looked serious.

Castiel swallowed, "Okay."

Dean's eyes averted back to his helmet and he spoke softly, "Thank you, and--- I'm sorry."

Blinking twice, Castiel shifted his weight to his other foot, not understanding.

"For what, exactly?"

"Picking on you," Dean let out a breath and his cheeks puffed out with it, he seemed heavy with his thoughts. "I shouldn't have-- it wasn't. Wasn't cool." He looked up again and met Castiel's eyes. "I am sorry."

It took him a moment, a tense moment, but he finally said, "I forgive you."

And Castiel meant it.

Dean's lip twitched up and he sheepishly looked down, bringing his leg over the bike and coming to stand up in front of Castiel. They were only a couple feet away.

"And, thank you for giving me a reason." He grinned adorably up at him.

Castiel felt his breath come faster and he spoke, "Giving you a reason for what?"

Dean's eyes sparkled and he whispered, "A reason to win."

And suddenly, Castiel understood that under the leather and the motorcycle and the roughness and the harsh way he bumped into Castiel in the hallways and the way he gripped lab tables, there was a soft, a gentle side to Dean Winchester he never seemed to look for before.

There it was, right in front of him as bright and clear as ever, Dean: the boy who was just desperate to connect. To connect with Castiel.

His heart soared forwards, closer to Dean, and he stepped forward twice and pushed his heels up, grabbed Dean's collar and pulled him down to softly press their lips together. Castiel felt a spark light up through his spine, spread throughout his body, and he felt complete.

Deans stiffened, probably surprised, and just when Castiel felt he was going to pull back, he turned his head down towards Castiel, kissed him again and set his hands on his waist, bringing his body closer.

Reluctantly, Castiel pulled away, but their faces were only a few inches apart and even in the dim light he could still make out the way Dean's smile came to his face in waves, making his eyes crease in the corners and he stared right at Castiel's soul. He realized that dazzling smile mirrored his own.

****

Castiel stepped down the steps of the school and the sunlight warmed his skin. He so wished there were more windows in the building to let in it, especially right at the beginning of summer, right before school ended.

Within days, he would no longer be a sophomore, but a junior starting the other half of his journey in a school that seemed so unfamiliar only months ago. Now it felt like home.

A low rumble pulled him out of his thoughts, as the motorcycle stopped right in front of him. He stepped down the last few steps to greet his boyfriend.

Dean was as handsome as ever as he took his helmet off, it glittered in the sunlight, and he smiled up at Castiel.

"Hey there."

His hair was pressed down from the helmet and Castiel reached over with a smile and ruffled it. Dean laughed loudly at him, a sound Castiel positively loved, and grabbed him closer so he was sitting right on top of the bike, his legs cramped together in front of him and Dean shuffled back slightly to give him more room, but Castiel didn't really mind being so close.

"Hi." he greeted back, shyly. Dean only leaned in closer, and Castiel's heart bloomed into a dove and flew high on the blue sky above them with happiness.

In a faraway corner of his mind, he remembered that he would have - should have - been scared to be this close to Dean and his leather jacket and award winning smile and fists that could punch a hole through the wall and a height that felt like he towered above Castiel and made him feel terrified and, frankly, pissed off at Dean's existence and obsession with annoying him to no end; but it was only a distant memory now.

It could never compare to the reliable safety he felt right now. The same feeling as the night of the race, when he kissed him.

"Shall we?" He raised his eyebrows, referring to their plans to drive around in the city and have a day of adventures, just the two of them.

The weather was perfect and they had no more schoolwork to do and Castiel simply couldn't wait. They switched spots on the bike and Castiel put his helmet on, a dark navy blue, a present from Dean shortly after they started dating. Castiel insisted on paying him back, but Dean just shut him up with kisses and sternly said that it was "to keep you safe when you ride with me."

"Absolutely." Castiel said from behind Dean now, his voice slightly muffled, the air already fogging inside the helmet from the heat around him. He wrapped his arms around Dean and he swore he could feel him smile.

"Just please-- you know," Castiel said warily, "watch where you're going."

Dean Winchester threw his head back and heartily chuckled to himself, then he pressed his foot down and Castiel lurched backwards from the speed of the bike, his hands held onto Dean tight.

He wasn't so bad after all.

**Notes for the Chapter:**

> AHHHHHHHHHHHHHHHHHHHHHH. Yup. That's it for this one. And for anyone wondering, yes: they stay together forever. Thanks for reading the longest fanfic I have EVER written (so far), I hope you liked it! Comment if BadBoy!Dean is as much your weakness as is mine and if I should write more of him ;)


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